title: Catalytic allylation of stabilized phosphonium ylides with primary allylic amines.
abstract: A range of ketone-stabilized phosphonium ylides were allylated with high regioselectivity by primary allylic amines in the presence of 5 mol % Pd(PPh3)4 and 10 mol % B(OH)3, and subsequent one-pot Wittig olefination gave structurally diverse α,β-unsaturated ketones in good to excellent overall yields with excellent E selectivity. The one-pot allylation/olefination reaction was extended to ester- and nitrile-stabilized phosphonium ylides by replacing B(OH)3 with TsOH, and the corresponding α,β-unsaturated esters and nitriles were obtained in moderate overall yields.
authors.affiliation: Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Xian-Tao
authors.initials: XT
authors.lastname: Ma
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
authors.forename: Rui-Han
authors.initials: RH
authors.lastname: Dai
authors.forename: Cong-Rong
authors.initials: CR
authors.lastname: Liu
authors.forename: Shi-Kai
authors.initials: SK
authors.lastname: Tian
mesh_terms: D000499:Allylamine / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D009570:Nitriles; D009943:Organophosphorus Compounds; D000499:Allylamine